Ether-like constituted compound



Patented Dec. 25, 1934 I I ETHER LIKE CONSTITUTED COlWPOUND HAVING WETTING, DISPERSING, EMULSI- FYING, AND WASHING PROPERTIES Adolf Steindoril, Karl Daimler, and Karl Plats,

Frankfort-on-the Main-Hochst, Germany, assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application April 9, 1931, Serial No. 528,974. In Germany April 17,1930

Claims. (C1. 260--151) The present invention relates to ether-like conbutylene and sulfuric anhydride, for instance stituted compounds having wetting, dispersing, with the use of liquid sulfur dioxide as a solvent. emulsifying nd a hing properties, As alcohols there 'may be 'used for example We have found that an aliphatic sulfonic cetyl alcohol, stearyl alcohol or oleic alcohol or 5 acid containing hydroxyl or halogen or a naphthenyl alcohol, mixtures of parafilnes and 5 derivative thereof having thegeneral formula: alcohols and the like, sterines, such as phytosterine or mixtures containing sterine, such as Z woolwax (a mixture of wool fat and alcohol);

instead of these alcohols there may likewise be v \z used oils or fats containing hydroxyl such as 10 wherein X may stand for SOaH, Y may stand 9 on or pydrotystearic acid ester and the for a substituent of the group consisting of i the reactlon being cqnductedi under OH Hos-H, halogen X and Y together may tions whereby sapomfication is avoided, so that stand for the group i only W alcoholic yd o yl roup of the fat 4O, enters into reaction. Aliphatic bodies contain- 16 mg several hydroxyl groups may likewise be used, for instance starch, cellulose, polyvinyl alcohol, poly-glycerin, partial saponification products of and Z may stand for H or alkyl may react with yl acetate and t like. Instead of the 20 an aliphatic body containing hydroxyl and p aforesaid aliphatic and other hydroxy-sulfonic 20 mg the general formula, acids or the derivatives thereof, there may be used halogen ethane-sulfonic acids, for instance R-OH chloro-ethane-sulfonic acid and the like. All

wherein R stands for a. hydrocarbon radicle, the assistants which are Suitable for P o g the molecule f which contains more than 3 carbon alkoxylation, for instance catalysts, metallic 26 atoms, with formation of an ether-like body sodium be usedwhich, due to its external sulfo-groups readily bodies, estel'iflcfltion p ucts of dissolves in acids and shows remarkable properaliphatic hydmalomatic acids of high 6011- ties when being used in the textile industry. The Weight and aliphatic or atic alco- 30 products obtained having the following formula: hols 0f high molecular i t may likewise be 30 Z treated with ethionic acid or with carbyl sulfate or with homologous and analogous aliphatic derivatives of sulfonic acid, whereby there are obwherein R1 stands for a hydrocarbon radical, the tained with simultaneous fission of the wax-like molecule of which contains more than 3 carbon esters, products of a mixed character which are 35 atoms and Z, "stands for H- or alkyl, and Me soluble in waterand acids. These mixed products stands for hydrogen, an alkali metal or amare excellently suitable as wetting agents, washmonium, possess a particularly strong foaming ing agents, dispersing agents, emulsifying agents power and an excellent soap-like action and at and the like.

4,0 the same time a high resistance to lime and they It could not have been foreseen that the reac- 40 are excellent wetting agents, dispersing agents, tion would take such a course, but it was to be emulsifying agents and washing agents. expected that under these conditions the wax- The process may, for instance, be conducted like esters could not be converted into the waterby combining the hydroxy-ethane-sulfonic acid soluble form. The process involves a particular or the homologue thereof with an aliphatic industrial advantage, because itis possible to work 45 alcohol of high molecular weight, for instance up in one operation both the alcoholic acid and with the aid of gaseous hydrochloric acid water the acidic components of the wax without isolatbeing split off. It may likewise be advantageous ing them. It is, therefore, unnecessary for into use carbyl sulfate or ethionic acid instead of stance first to liberate the alcohols from the hydroxyethane-sulfonic acid or a salt thereof, waxes, to isolate them and then to work them up. 50 the reaction occurring much more quickly owing The present process may advantageously be apto the sulfuric acid which is liberated during the plied for working up in an easy and economical reaction. Instead of the carbyl sulfate there may manner so as to obtain valuable wetting agents, be used homologous products which can be obcheap products such as thewax-like esters which tained, for instance, from bu yl a o ol or are obtainable bythe oxidation of parafiin or the 55 wax mixtures known as wool fat. The process may likewise be successfully applied to vegetable waxes, such as Japanese wax, carnauba wax and to fossil waxes, such as Montan wax and the bleached products therefrom. Among the insect waxes beeswax may be particularly mentioned as a suitable starting material. Instead of ethionic acid or carbyl sulfate there may be used analogous products obtainable from alcohols of .high molecular weight or from poly alcohols with sulfur trioxide, and the like.

The following examples serve to illustrate our invention, but they are not intended to limit it thereto, the parts being by weight:

(1) 270 parts of stearyl alcohol are introduced in the course of 1 hour at a temperature between 40 C. and 50 G. into 206 parts of ethionic acid,

, while stirring. Stirring is continued at this temperature until a test sampleis soluble in water to a clear solution. The product obtained which is presumed to be the sulfonic acid of ethyl-stearyl ether is converted into its ammonium salt or sodium salt and in this form constitutes an excellent substitute for soap.

(2) 100 parts of cotton are kneaded in a mixing and kneading machine ata temperature between about C. and 40 0. together with 30 parts of .ethionic acid. There is obtained a water-soluble product, which after neutralization can be used as an assistant in the'textileindustry, for instance as sizing agent and the like.

(3) Into a solution of parts of naphthenyl alcohol in benzene 23 parts of sodium in the form of slices are introduced. The mixture is stirred at a raised temperature until the sodium has completely dissolved. In the course of 1 hour'21'0 parts of sodium chloroethane sulfonate (of '80 per cent. strength) are added and the whole is boiled for 4 hours in a reflux apparatus. The benzene is then removed by distillation and 2'70 parts of water are added while well stirring. The product is obtained in the form of a solutionof about 50 per cent. strength which is suitable for use as a wetting agent in concentrated alkali solutions and acids.

(4) 126 parts of hydroxy-ethane-sulfonic acid are caused to run into 1'75 parts of a mixture of alcohols obtainable by the hydrogenation of coconut oil. The mixture is stirred for 5 hours at a temperature between C. and C. and the reaction product is then soluble in hot water to a clear solution. The solutions of the product have a great foaming power; they have to a marked extent the property of reducing the surface tension and therefore they can advantageously be used as wetting agents in the branches.

obtainable by treating n-butyl-alcohol with S03.

(5) 150 parts of ethionic acid are added, while stirring, in the course of 1 hour to 150 parts of spermaceti at a temperature between 50 C. and 60 C. and the mixture is kept for some time at this temperature. The product obtained solidifies in the cold and dissolves in hot water to a soand 60 ,C. The mixture is-stirred at this temperaturerfor 15-20 hours and .neutralized in a kneading machine with 36 parts of sodium carbonate while simultaneously adding 40 parts of water. There are thus obtained 186 parts of a paste which is soluble in hot water toa nearly clear solution and which can be used for scrooping artificial silk and. for dressing purposes.

7 50 parts of ethionic acid are caused to run into 60 parts of molten Japanese wax at a temperature between 50 C. and 60 C. as it is described in Example 6. The reaction and working up are conducted as described in the foregoing example. The product obtained is particularly-suitable for use as a carrier in the preparation of paraffin emulsions.

(8) '74 parts of butyl alcohol and 126' parts of hydroxy-ethane-sulfonic acid are caused to react as described in Example 4. There is obtained a wetting agent which is stable in the strongest alkali solutions and can be used with particular advantage for mercerization.

We claim:

1. The compounds of the following formula:

having a particularly strong foaming power and an excellent soap-like action and simultaneously an intense resistance to lime.

3. The compounds of the following formula:

wherein R1 stands for an aliphatic hydrocarbon radical, the molecule of which contains more than 3 carbon atoms and Me stands for hydrogen. an alkali metal or ammonium, having a particularly strong foaming power and an excellent soap-like action and simultaneously an intense resistance to lime. i

4. The compound of the following formula:

having a particularly strong foaming power and an excellent soap-like action and simultaneously an intense resistance to lime.

5. The compound of the following formula:

wherein R1 stands for the aliphatic radical of the alcohols obtainable by the hydrogenation of coconut oil, having a particularly strong foaming power and an excellent soap-like action and simultaneously an intense resistance to lime.

ADOLF STEINDORFF. KARL DAIMLER. KARL PLATZ. 

